Sodium Hydroxide → 2-[4-(2,4-Dichlorobenzoyl)benzyl]thio-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

HRID 1291279Notes

Reaction equation

HRID 1291279 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7]([SH:12])=[N:6][C:5]=2[NH:4][CH:3]=1.[OH-].[Na+].[Cl:15][C:16]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:17]=1[C:18]([C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1)=[O:19]>CO.COCCOC>[Cl:15][C:16]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:17]=1[C:18]([C:20]1[CH:21]=[CH:22][C:23]([CH2:24][S:12][C:7]2[NH:8][C:9](=[O:11])[C:10]3[C:2]([CH3:1])=[CH:3][NH:4][C:5]=3[N:6]=2)=[CH:26][CH:27]=1)=[O:19]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 189192794-(2,4-Dichlorobenzoyl)benzyl bromideHCID 178430835HCID 178430835, compound

Product 1

HCID 1356675872-[4-(2,4-Dichlorobenzoyl)benzyl]thio-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-oneYield 60.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

In methanol (18.7 ml) was suspended 5-methyl-2-mercapto-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (1.36 g) followed by addition of 1N-sodium hydroxide (7.88 ml) for dissolution. Then, under ice-cooling, a solution of 4-(2,4-dichlorobenzoyl)benzyl bromide (3.09 g) in DME (8 ml) was added dropwise. The mixture was stirred at room temperature for 4 hours and the resulting crystalline precipitate was collected by filtration and rinsed with water. The crystals were further rinsed with 50% ethanol/water, methanol and ether, dried, and recrystallized from DME (1,2-dimethoxyethane) to provide the title compound (2.03 g). 1H-NMR (DMSO-d6) δ: 2.23(3H,s), 4.48(2H,s), 6.65(1H,s), 7.53(1H,d,J=8.2Hz), 7.59(1H,dd,J=1.6,8.8Hz), 7.64(2H,d,J=8.4Hz), 7.69(2H,d,J=8.4Hz), 7.80(1H,d,J=1.6Hz), 11.40(1H,s), 11.96(1H,s).

Workup

  1. temperatureThen, under ice-cooling
  2. filtrationthe resulting crystalline precipitate was collected by filtration
  3. washrinsed with water
  4. washThe crystals were further rinsed with 50% ethanol/water, methanol and ether
  5. customdried
  6. customrecrystallized from DME (1,2-dimethoxyethane)

Sources & evidence

ORD record
ord-58d35f016b07460b9234bfc8207dc36f
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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